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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
2-bromo-4-chloro-6-fluoropyridine-3,5-d2 2-bromo-4-chloro-6-fluoropyridine-3,5-d2 2460494-27-1 C5BrClD2FN
2-chloro-4,5-bis(methyl-d3)pyridine-3,6-d2 2-chloro-4,5-bis(methyl-d3)pyridine-3,6-d2 2460491-59-0 C7ClD8N
6-(methyl-d3)pyridin-3,4,5-d3-2-ol 6-(methyl-d3)pyridin-3,4,5-d3-2-ol 916979-14-1 C6HD6NO
3,4-bis(methyl-d3)pyridin-2(1H)-one-5,6-d2 3,4-bis(methyl-d3)pyridin-2(1H)-one-5,6-d2 2460501-15-7 C7HD8NO
2-(4-bromo-3-(methyl-d3)-1H-pyrazol-1-yl-5-d)pyridine-3,4,5,6-d4 2-(4-bromo-3-(methyl-d3)-1H-pyrazol-1-yl-5-d)pyridine-3,4,5,6-d4 2460493-87-0 C9BrD8N3
4-bromo-2-(1H-imidazol-2-yl-4,5-d2)pyrimidine 4-bromo-2-(1H-imidazol-2-yl-4,5-d2)pyrimidine 2256714-03-9 C7H3BrD2N4
1-(6-(methyl-d3)pyridin-3-yl-2,4,5-d3)ethan-1-one-2,2,2-d3 1-(6-(methyl-d3)pyridin-3-yl-2,4,5-d3)ethan-1-one-2,2,2-d3 2600399-13-9 C8D9NO
6-(cyclopropyl-d5)pyridin-3-amine 6-(cyclopropyl-d5)pyridin-3-amine 2600400-60-8 C8H5D5N2
3-bromo-5-(cyclopropyl-d5)pyridine 3-bromo-5-(cyclopropyl-d5)pyridine 2600400-68-6 C8H3BrD5N
4-bromo-2-(cyclopropyl-d5)pyridine-3,5,6-d3 4-bromo-2-(cyclopropyl-d5)pyridine-3,5,6-d3 2600400-18-6 C8BrD8N
6-(cyclopropyl-d5)pyridin-3,4,5-d3-2-ol 6-(cyclopropyl-d5)pyridin-3,4,5-d3-2-ol 2600399-71-9 C8HD8NO
pyrimidin-d3-4-amine pyrimidin-d3-4-amine 2600400-46-0 C4H2D3N3
4-chloro-2-(cyclopropyl-d5)pyrimidine-5,6-d2 4-chloro-2-(cyclopropyl-d5)pyrimidine-5,6-d2 2600400-72-2 C7ClD7N2
2-(methyl-d3)pyrimidin-5,6-d2-4-amine 2-(methyl-d3)pyrimidin-5,6-d2-4-amine 2600399-56-0 C5H2D5N3
2,8-bis(methyl-d3)imidazo[1,2-b]pyridazin-3,7-d2-6-ol 2,8-bis(methyl-d3)imidazo[1,2-b]pyridazin-3,7-d2-6-ol 2645416-15-3 C8HD8N3O
6-bromo-8-(methyl-d3)imidazo[1,2-b]pyridazine-2,3,7-d3 6-bromo-8-(methyl-d3)imidazo[1,2-b]pyridazine-2,3,7-d3 2645419-42-5 C7BrD6N3
1-(4-bromo-6-(methoxy-d3)pyridin-2-yl-3,5-d2)ethan-1-one-2,2,2-d3 1-(4-bromo-6-(methoxy-d3)pyridin-2-yl-3,5-d2)ethan-1-one-2,2,2-d3 2645413-23-4 C8BrD8NO2
2-bromo-4,6-difluoropyridine-3,5-d2 2-bromo-4,6-difluoropyridine-3,5-d2 2645416-49-3 C5BrD2F2N
5-aminopyridin-2,4,6-d3-3-ol 5-aminopyridin-2,4,6-d3-3-ol 2645412-05-9
5-amino-4-bromopyridin-2,6-d2-3-ol 5-amino-4-bromopyridin-2,6-d2-3-ol 2645417-24-7 C5H3BrD2N2O
5-bromo-2-(methyl-d3)pyridine 5-bromo-2-(methyl-d3)pyridine 1185312-36-0 C6H3BrD3N
2-(methyl-d3)pyrimidin-4(3H)-one-5,6-d2 2-(methyl-d3)pyrimidin-4(3H)-one-5,6-d2 2645412-80-0 C5HD5N2O
2-chloro-4-(methyl-d3)-5-(trifluoromethyl)pyrimidine-6-d 2-chloro-4-(methyl-d3)-5-(trifluoromethyl)pyrimidine-6-d 2645412-66-2 C6ClD4F3N2
6-bromo-1-(methyl-d3)pyridin-2(1H)-one 6-bromo-1-(methyl-d3)pyridin-2(1H)-one 2645419-29-8 C6H3BrD3NO
3,5-bis(methyl-d3)-2-(trifluoromethyl)pyridin-4-amine 3,5-bis(methyl-d3)-2-(trifluoromethyl)pyridin-4-amine 2645417-26-9 C8H3D6F3N2
2,3-bis(methyl-d3)pyridin-4-amine 2,3-bis(methyl-d3)pyridin-4-amine 2645417-43-0 C7H4D6N2
2-((azetidin-3-yl-2,2,3,4,4-d5)oxy)-4-bromopyridine 2-((azetidin-3-yl-2,2,3,4,4-d5)oxy)-4-bromopyridine 2645419-66-3 C8H4BrD5N2O
2-((azetidin-3-yl-2,2,3,4,4-d5)oxy)-6-bromopyridine 2-((azetidin-3-yl-2,2,3,4,4-d5)oxy)-6-bromopyridine 2645416-63-1 C8H4BrD5N2O
2-bromo-5-(2-methoxyethoxy)pyridine-3,4,6-d3 2-bromo-5-(2-methoxyethoxy)pyridine-3,4,6-d3 2645417-55-4 C8H7BrD3NO2
4-bromo-2-(methoxymethyl)pyridine-3,5,6-d3 4-bromo-2-(methoxymethyl)pyridine-3,5,6-d3 2645415-67-2 C7H5BrD3NO
2-bromo-4-(methoxymethyl)pyridine-3,5,6-d3 2-bromo-4-(methoxymethyl)pyridine-3,5,6-d3 2645415-69-4 C7H5BrD3NO
6-((methoxy-d3)methyl-d2)pyridin-2,4,5-d3-3-amine 6-((methoxy-d3)methyl-d2)pyridin-2,4,5-d3-3-amine 2645416-74-4 C7H2D8N2O
4-bromo-2-((methoxy-d3)methyl-d2)pyrimidine-5,6-d2 4-bromo-2-((methoxy-d3)methyl-d2)pyrimidine-5,6-d2 2645418-73-9 C6BrD7N2O
3,5-dibromopyrazolo[1,5-a]pyrimidine-2,6,7-d3 3,5-dibromopyrazolo[1,5-a]pyrimidine-2,6,7-d3 2645415-89-8 C6Br2D3N3
imidazo[1,2-a]pyridin-d5-8-amine imidazo[1,2-a]pyridin-d5-8-amine 2645413-72-3 C7H2D5N3
2,4-dibromo-6-(methyl-d3)pyridine 2,4-dibromo-6-(methyl-d3)pyridine 2645418-96-6 C6H2Br2D3N
2-bromo-5-methylpyridine-3,4,6-d3 2-bromo-5-methylpyridine-3,4,6-d3 2645412-94-6 C6H3BrD3N
6-methylpyridin-3,4,5-d3-2-ol 6-methylpyridin-3,4,5-d3-2-ol 2645412-98-0 C6H4D3NO
2-methylpyridin-4,5,6-d3-3-ol 2-methylpyridin-4,5,6-d3-3-ol 2645416-82-4 C6H4D3NO
2-bromo-N-(methyl-d3)pyridin-4-amine 2-bromo-N-(methyl-d3)pyridin-4-amine 2645419-89-0 C6H4BrD3N2
6-bromo-N-methylpyridin-2,4,5-d3-3-amine 6-bromo-N-methylpyridin-2,4,5-d3-3-amine 2645415-81-0 C6H4BrD3N2
tert-butyl 4-(4-hydroxypyridin-2-yl)piperazine-1-carboxylate-2,2,3,3,5,5,6,6-d8 tert-butyl 4-(4-hydroxypyridin-2-yl)piperazine-1-carboxylate-2,2,3,3,5,5,6,6-d8 2645413-12-1 C14H13D8N3O3
tert-butyl tetrahydropyrimidine-1(2H)-carboxylate-2,2,4,4,5,5,6,6-d8 tert-butyl tetrahydropyrimidine-1(2H)-carboxylate-2,2,4,4,5,5,6,6-d8 2697162-41-5 C9H10D8N2O2
1H-pyrrolo[2,3-c]pyridine-2,3,4,5,7-d5 1H-pyrrolo[2,3-c]pyridine-2,3,4,5,7-d5 2697155-51-2 C7HD5N2
3-bromo-5-fluoro-2-(methyl-d3)pyridine-4,6-d2 3-bromo-5-fluoro-2-(methyl-d3)pyridine-4,6-d2 2645415-74-1 C6BrD5FN
tert-butyl 4-(5-bromopyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate tert-butyl 4-(5-bromopyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate 2697155-08-9 C15H18BrD3N2O2
tert-butyl 4-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate tert-butyl 4-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate 2697162-81-3 C15H18BrD3N2O2
2-bromo-6-(tetrahydro-2H-pyran-4-yl)pyridine-3,4,5-d3 2-bromo-6-(tetrahydro-2H-pyran-4-yl)pyridine-3,4,5-d3 2697156-29-7 C10H9BrD3NO
2-bromo-4-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 2-bromo-4-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 2697156-23-1 C10H7BrD5NO
2-bromo-4-(tetrahydro-2H-pyran-4-yl)pyrimidine-5,6-d2 2-bromo-4-(tetrahydro-2H-pyran-4-yl)pyrimidine-5,6-d2 2697163-15-6 C9H9BrD2N2O
4-chloro-2,6-bis(methyl-d3)pyrimidine-5-d 4-chloro-2,6-bis(methyl-d3)pyrimidine-5-d 2697162-88-0 C6ClD7N2
2,6-bis(methyl-d3)pyrimidin-4-amine 2,6-bis(methyl-d3)pyrimidin-4-amine 2697155-71-6 C6H3D6N3
5-(trifluoromethyl)pyridin-2,4,6-d3-3-ol 5-(trifluoromethyl)pyridin-2,4,6-d3-3-ol 2697156-91-3 C6HD3F3NO
4-bromo-3-methoxypyridine-2,5,6-d3 4-bromo-3-methoxypyridine-2,5,6-d3 2697156-52-6 C6H3BrD3NO
2-(ethyl-d5)-6-fluoropyridine-3,4,5-d3 2-(ethyl-d5)-6-fluoropyridine-3,4,5-d3 2697156-97-9 C7D8FN
6-(ethyl-d5)pyridin-2,4,5-d3-3-amine 6-(ethyl-d5)pyridin-2,4,5-d3-3-amine 2697156-62-8 C7H2D8N2
4-bromo-3,5-dimethylpyridine-2,6-d2 4-bromo-3,5-dimethylpyridine-2,6-d2 2697162-95-9 C7H6BrD2N
2,4-dibromo-3-(methoxy-d3)pyridine 2,4-dibromo-3-(methoxy-d3)pyridine 2697162-99-3 C6H2Br2D3NO
6-(difluoromethyl-d)pyridin-2,4,5-d3-3-ol 6-(difluoromethyl-d)pyridin-2,4,5-d3-3-ol 2697163-00-9 C6HD4F2NO
3-bromo-2-(difluoromethyl-d)-5-(methoxy-d3)pyridine-4,6-d2 3-bromo-2-(difluoromethyl-d)-5-(methoxy-d3)pyridine-4,6-d2 2711075-20-4 C7BrD6F2NO
5'-bromo-[2,2'-bipyridin]-3,3',4,4',6,6'-d6-5-ol 5'-bromo-[2,2'-bipyridin]-3,3',4,4',6,6'-d6-5-ol 2711075-31-7 C10HBrD6N2O
tert-butyl 3-(4-bromopyridin-2-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(4-bromopyridin-2-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768655-38-3 C15H12BrD9N2O2
tert-butyl 3-(2-bromopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(2-bromopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768657-44-7 C15H9BrD12N2O2
tert-butyl 3-(5-aminopyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-aminopyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768654-94-8 C15H11D12N3O2
pyridine-3,4-dicarboxylic-d3 acid pyridine-3,4-dicarboxylic-d3 acid 2768654-77-7 C7H2D3NO4
5-bromo-2-fluoro-3-(methyl-d3)pyridine 5-bromo-2-fluoro-3-(methyl-d3)pyridine 2256740-03-9
4-bromo-5-(methyl-d3)pyridin-3,6-d2-2-amine 4-bromo-5-(methyl-d3)pyridin-3,6-d2-2-amine 2256740-14-2 C6H2BrD5N2
3-chloro-4-(methyl-d3)pyridin-2-ol 3-chloro-4-(methyl-d3)pyridin-2-ol 2768657-53-8 C6H3ClD3NO
2-chloro-6-(methoxy-d3)pyridin-4-amine 2-chloro-6-(methoxy-d3)pyridin-4-amine 2806720-39-6 C6H4ClD3N2O
4-bromo-3-(trifluoromethyl)pyridine-2,5,6-d3 4-bromo-3-(trifluoromethyl)pyridine-2,5,6-d3 2806728-79-8 C6BrD3F3N
2-chloro-5-(ethyl-d5)pyridin-3,6-d2-4-amine 2-chloro-5-(ethyl-d5)pyridin-3,6-d2-4-amine 2806720-26-1 C7H2ClD7N2
3-bromo-2-chloropyridin-5,6-d2-4-amine 3-bromo-2-chloropyridin-5,6-d2-4-amine 2806721-39-9 C5H2BrClD2N2
3-bromo-4-(trifluoromethyl)pyridine-2,5,6-d3 3-bromo-4-(trifluoromethyl)pyridine-2,5,6-d3 2806721-24-2 C6BrD3F3N
3-cyclopropyl-2-(methyl-d3)pyridin-5,6-d2-4-amine 3-cyclopropyl-2-(methyl-d3)pyridin-5,6-d2-4-amine 2806719-76-4 C9H7D5N2
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-2,5,6-d3 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-2,5,6-d3 2806718-65-8 C6HClD3N3
2,5-bis(methyl-d3)-6-(trifluoromethyl)pyridin-4-d-3-ol 2,5-bis(methyl-d3)-6-(trifluoromethyl)pyridin-4-d-3-ol 2826916-34-9 C8HD7F3NO
3,5-dibromo-2-(methyl-d3)pyridine 3,5-dibromo-2-(methyl-d3)pyridine 2826917-11-5 C6H2Br2D3N
5-bromo-3-(methoxy-d3)-2-(methyl-d3)pyridine-4,6-d2 5-bromo-3-(methoxy-d3)-2-(methyl-d3)pyridine-4,6-d2 2826917-18-2 C7BrD8NO
5-(methoxy-d3)-6-(methyl-d3)pyridin-2,4-d2-3-amine 5-(methoxy-d3)-6-(methyl-d3)pyridin-2,4-d2-3-amine 2826916-88-3 C7H2D8N2O
4-bromo-3-fluoro-2-(methyl-d3)pyridine 4-bromo-3-fluoro-2-(methyl-d3)pyridine 2826917-46-6 C6H2BrD3FN
4-bromo-2-(fluoromethyl-d2)pyridine-3,5,6-d3 4-bromo-2-(fluoromethyl-d2)pyridine-3,5,6-d3 2891512-04-0 C6BrD5FN
5-bromo-2-(fluoromethyl)pyridine-3,4,6-d3 5-bromo-2-(fluoromethyl)pyridine-3,4,6-d3 2891520-25-3 C6H2BrD3FN
4-bromo-2-(methyl-d3)-3-(trifluoromethyl)pyridine-5,6-d2 4-bromo-2-(methyl-d3)-3-(trifluoromethyl)pyridine-5,6-d2 2891518-55-9 C7BrD5F3N
6-(methyl-d3)-5-(trifluoromethyl)pyridin-3-ol 6-(methyl-d3)-5-(trifluoromethyl)pyridin-3-ol 2891520-77-5 C7H3D3F3NO
6-(methyl-d3)-5-(trifluoromethyl)pyridin-3,4-d2-2-amine 6-(methyl-d3)-5-(trifluoromethyl)pyridin-3,4-d2-2-amine 2891512-35-7 C7H2D5F3N2
5-(methyl-d3)-6-(trifluoromethyl)pyridin-2-ol 5-(methyl-d3)-6-(trifluoromethyl)pyridin-2-ol 2891519-07-4 C7H3D3F3NO
4-(methyl-d3)-6-(trifluoromethyl)pyridin-3,5-d2-2-amine 4-(methyl-d3)-6-(trifluoromethyl)pyridin-3,5-d2-2-amine 2891517-21-6 C7H2D5F3N2
3-bromo-2-methyl-6-(trifluoromethyl)pyridine-4,5-d2 3-bromo-2-methyl-6-(trifluoromethyl)pyridine-4,5-d2 2891512-45-9 C7H3BrD2F3N
2-bromo-3-(methyl-d3)-6-(trifluoromethyl)pyridine-4,5-d2 2-bromo-3-(methyl-d3)-6-(trifluoromethyl)pyridine-4,5-d2 2891520-81-1 C7BrD5F3N
5-bromo-2-(1,1-difluoroethyl)pyridine-3,4,6-d3 5-bromo-2-(1,1-difluoroethyl)pyridine-3,4,6-d3 2891520-08-2 C7H3BrD3F2N
3-bromo-2-(1,1-difluoroethyl-2,2,2-d3)pyridine 3-bromo-2-(1,1-difluoroethyl-2,2,2-d3)pyridine 2891518-51-5 C7H3BrD3F2N
5-bromo-2-(1,1-difluoroethyl)pyrimidine-4,6-d2 5-bromo-2-(1,1-difluoroethyl)pyrimidine-4,6-d2 2891512-68-6 C6H3BrD2F2N2
2,6-dibromo-3-(methyl-d3)pyridine 2,6-dibromo-3-(methyl-d3)pyridine 2891521-27-8 C6H2Br2D3N
3-bromo-2-(methoxy-d2)pyridine 3-bromo-2-(methoxy-d2)pyridine 2891520-51-5 C6H4BrD2NO
2-bromo-3-(methoxy-d2)pyridine-4,5,6-d3 2-bromo-3-(methoxy-d2)pyridine-4,5,6-d3 2891512-82-4 C6HBrD5NO
4-bromo-2-(methoxy-d2)pyrimidine 4-bromo-2-(methoxy-d2)pyrimidine 2891518-76-4 C5H3BrD2N2O
3-chloro-6-(methoxy-d2)pyridazine 3-chloro-6-(methoxy-d2)pyridazine 2891518-78-6 C5H3ClD2N2O
3-bromo-2-methyl-5-(trifluoromethyl)pyridine-4,6-d2 3-bromo-2-methyl-5-(trifluoromethyl)pyridine-4,6-d2 2891518-81-1 C7H3BrD2F3N
4-chloro-1H-pyrrolo[2,3-d]pyridazine-2,3,7-d3 4-chloro-1H-pyrrolo[2,3-d]pyridazine-2,3,7-d3 2891521-09-6 C6HClD3N3
5,6-dibromopyridin-2,4-d2-3-ol 5,6-dibromopyridin-2,4-d2-3-ol 2891512-74-4 C5HBr2D2NO
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